Ink, ink cartridge, ink jet recording device, ink jet ink printed matter, compound, and composition

ABSTRACT

Ink contains at least one of a compound represented by the following chemical formula 1, a compound represented by chemical formula 2, a compound represented by chemical formula 3, or a compound represented by chemical formula 4.

CROSS-REFERENCE TO RELATED APPLICATIONS

This patent application is based on and claims priority pursuant to 35U.S.C. § 119 to Japanese Patent Application Nos. 2013-118869 and2014-057602, on Jun. 5, 2013 and Mar. 20, 2014, respectively, in theJapan Patent Office, the entire disclosures of which are herebyincorporated by reference herein.

BACKGROUND

Technical Field

The present invention relates to ink, an ink cartridge, an ink jetrecording device, an ink jet ink printed matter, a compound, and acomposition.

Background Art

An ink jet recording system is known as a method of forming an image ona recording medium, typically paper. The ink jet recording system has anexcellent consumption efficiency and excellent resource savingproperties, resulting in low cost of ink per recording unit.

In recent years, ink jet recording system using ultraviolet curing inkhas become appealing.

JP-2009-67926-A discloses an ink composition for ink jet recording andthe ink composition contains: (A) aliphatic(meth)acrylate compoundhaving a secondary hydroxyl group; (B): a compound having a nitrogenatom and a polymerizable unsaturated bond in its molecule; and (C): aradical polymerization initiator.

JP2009-144057-A discloses an ink composition for ink jet recordingcontaining: (A): a polymerizable compound and (B): a radicalpolymerization initiator. As the polymerizable compound (A) contains apolymerizable compound (A1) having a polymerizable unsaturated bond andan amino group in its molecule. In addition, the ratio of amono-functional polymerizable monomer to the total amount of thepolymerizable compound (A) ranges from 90% by weight to 99.9% by weightand the ratio of a multi-functional monomer to the total amount of thepolymerizable compound (A) ranges from 0.1% by weight to 10% by weight.

Although these are successful to some degree, a compound havingexcellent polymerization property and photocurability with less odor andsmall viscosity is demanded.

SUMMARY

The present invention provides an improved Ink that contains at leastone of a compound represented by chemical formula 1, a compoundrepresented by chemical formula 2, a compound represented by chemicalformula 3, and a compound represented by chemical formula 4

where R₁ represents a hydrocarbon group having 1 to 10 carbon atoms andR₂ represents a monovalent group containing a group represented by —OX₁,where X₁ represents a monovalent hydrocarbon group having 1 to 10 carbonatoms, a monovalent group containing a group represented by —COOX₂,where X₂ represents a monovalent hydrocarbon group having 1 to 10 carbonatoms, a monovalent group containing a group represented by —OCOX₃,where X₃ represents a monovalent hydrocarbon group having 1 to 10 carbonatoms, a monovalent group containing a group represented by —NX₄X₅,where X₄ and X₅ each, independently represent monovalent hydrocarbongroups having 1 to 10 carbon atoms, a monovalent group containing agroup represented by —CONX₆X₇, where X₆ and X₇ each, independentlyrepresent monovalent hydrocarbon groups having 1 to 10 carbon atoms, ora monovalent group containing a hydroxyl group,

where, R₃ and R₄ each, independently represent monovalent groupscontaining groups represented by —OX₁, where X₁ represents a monovalenthydrocarbon group having 1 to 10 carbon atoms, a monovalent groupcontaining a group represented by —COOX₂, where X₂ represents amonovalent hydrocarbon group having 1 to 10 carbon atoms, a monovalentgroup containing a group represented by —OCOX₃, where X₃ represents amonovalent hydrocarbon group having 1 to 10 carbon atoms, a monovalentgroup containing a group represented by —NX₄X₅, where X₄ and X₅ each,independently represent monovalent hydrocarbon groups having 1 to 10carbon atoms, a monovalent group containing a group represented by—CONX₆X₇, where X₆ and X₇ each, independently represent monovalenthydrocarbon groups having 1 to 10 carbon atoms, or a monovalent groupcontaining a hydroxyl group,

where the ring A represents a saturated five-membered ring or asaturated six-membered ring, both containing a nitrogen atom, R₅represents a monovalent group containing a group represented by —OX₁,where X₁ represents a monovalent hydrocarbon group having 1 to 10 carbonatoms, a monovalent group containing a group represented by —COOX₂,where X₂ represents a monovalent hydrocarbon group having 1 to 10 carbonatoms, a monovalent group containing a group represented by —OCOX₃,where X₃ represents a monovalent hydrocarbon group having 1 to 10 carbonatoms, a monovalent group containing a group represented by —NX₄X₅,where X₄ and X₅ each, independently represent monovalent hydrocarbongroups having 1 to 10 carbon atoms, a monovalent group containing agroup represented by —CONX₆X₇, where X₆ and X₇ each, independentlyrepresent monovalent hydrocarbon groups having 1 to 10 carbon atoms, ora monovalent group containing a hydroxyl group, and a is 1, 2, or 3, and

where the ring B represents a saturated five-membered ring or asaturated six-membered ring, both containing two nitrogen atoms, R₆represents a monovalent group containing a group represented by —OX₁,where X₁ represents a monovalent hydrocarbon group having 1 to 10 carbonatoms, a monovalent group containing a group represented by —COOX₂,where X₂ represents a monovalent hydrocarbon group having 1 to 10 carbonatoms, a monovalent group containing a group represented by —OCOX₃,where X₃ represents a monovalent hydrocarbon group having 1 to 10 carbonatoms, a monovalent group containing a group represented by —NX₄X₅,where X₄ and X₅ each, independently represent monovalent hydrocarbongroups having 1 to 10 carbon atoms, a monovalent group containing agroup represented by —CONX₆X₇, where X₆ and X₇ each, independentlyrepresent monovalent hydrocarbon groups having 1 to 10 carbon atoms, amonovalent group containing a hydroxyl group, or an alkyl group having 1to 10 carbon atoms.

BRIEF DESCRIPTION OF THE DRAWINGS

Various other objects, features and attendant advantages of the presentinvention will be more fully appreciated as the same becomes betterunderstood from the detailed description when considered in connectionwith the accompanying drawings in which like reference charactersdesignate like corresponding parts throughout and wherein:

FIG. 1 is a diagram illustrating an example of the ink cartridgeaccording to an embodiment of the present invention; and

FIG. 2 is a diagram illustrating a printing mechanism of an ink jetrecording device to describe the entire configuration of the ink jetrecording device.

DETAILED DESCRIPTION

The present invention is to provide a compound and ink and a compositionthat contain the ink, which have excellent polymerization property andphotocurability with less odor and low viscosity

Next, embodiments of the present disclosure are described with referenceto accompanying drawings.

The ink of the present disclosure contains at least one of a compoundrepresented by chemical formula 1, a compound represented by chemicalformula 2, a compound represented by chemical formula 3, and a compoundrepresented by chemical formula 4.

In chemical formula 1, R₁ represents a hydrocarbon group having 1 to 10carbon atoms and R₂ represents a monovalent group containing a grouprepresented by —OX₁, where X₁ represents a monovalent hydrocarbon grouphaving 1 to 10 carbon atoms, a monovalent group having a grouprepresented by —COOX₂, where X₂ represents a monovalent hydrocarbongroup having 1 to 10 carbon atoms, a monovalent group having a grouprepresented by —OCOX₃, where X₃ represents a monovalent hydrocarbongroup having 1 to 10 carbon atoms, a monovalent group having a grouprepresented by —NX₄X₅, where X₄ and X₅ each, independently representmonovalent hydrocarbon groups having 1 to 10 carbon atoms, a monovalentgroup containing a group represented by —CONX₆X₇, where X₆ and X₇ each,independently represent monovalent hydrocarbon groups having 1 to 10carbon atoms, or a monovalent group containing a hydroxyl group.

In chemical formula 2, R₃ and R₄ each, independently representmonovalent groups containing groups represented by —OX₁, where X₁represents a monovalent hydrocarbon group having 1 to 10 carbon atoms, amonovalent group having a group represented by —COOX₂, where X₂represents a monovalent hydrocarbon group having 1 to 10 carbon atoms, amonovalent group having a group represented by —OCOX₃, where X₃represents a monovalent hydrocarbon group having 1 to 10 carbon atoms, amonovalent group having a group represented by —NX₄X₅, where X₄ and X₅each, independently represent monovalent hydrocarbon groups having 1 to10 carbon atoms, a monovalent group containing a group represented by—CONX₆X₇, where X₆ and X₇ each, independently represent monovalenthydrocarbon groups having 1 to 10 carbon atoms, or a monovalent groupcontaining a hydroxyl group.

In chemical formula 3, the ring A represents a saturated five-memberedring or a saturated six-membered ring, both containing a nitrogen atom,R₅ represents a monovalent group containing a group represented by —OX₁,where X₁ represents a monovalent hydrocarbon group having 1 to 10 carbonatoms, a monovalent group having a group represented by —COOX₂, where X₂represents a monovalent hydrocarbon group having 1 to 10 carbon atoms, amonovalent group having a group represented by —OCOX₃, where X₃represents a monovalent hydrocarbon group having 1 to 10 carbon atoms, amonovalent group having a group represented by —NX₄X₅, where X₄ and X₅each, independently represent monovalent hydrocarbon groups having 1 to10 carbon atoms, a monovalent group containing a group represented by—CONX₆X₇, where X₆ and X₇ each, independently represent monovalenthydrocarbon groups having 1 to 10 carbon atoms, or a monovalent groupcontaining a hydroxyl group, and a is 1, 2, or 3.

In chemical formula 4, the ring B represents a saturated five-memberedring or a saturated six-membered ring, both containing two nitrogenatoms, R₆ represents a monovalent group containing a group representedby —OX₁, where X₁ represents a monovalent hydrocarbon group having 1 to10 carbon atoms, a monovalent group having a group represented by—COOX₂, where X₂ represents a monovalent hydrocarbon group having 1 to10 carbon atoms, a monovalent group having a group represented by—OCOX₃, where X₃ represents a monovalent hydrocarbon group having 1 to10 carbon atoms, a monovalent group containing a group represented by—NX₄X₅, where X₄ and X₅ each, independently represent monovalenthydrocarbon groups having 1 to 10 carbon atoms, a monovalent groupcontaining a group represented by —CONX₆X₇, where X₆ and X₇ each,independently represent monovalent hydrocarbon groups having 1 to 10carbon atoms, a monovalent group containing a hydroxyl group, or analkyl group having 1 to 10 carbon atoms.

The compound represented by chemical formula 1, the compound representedby chemical formula 2, the compound represented by chemical formula 3,and the compound represented by chemical formula 4 have no carbonylimino group (—CONH—) but a monovalent group having a group representedby —OX₁, where X₁ represents a monovalent hydrocarbon group having 1 to10 carbon atoms, a monovalent group having a group represented by—COOX₂, where X₂ represents a monovalent hydrocarbon group having 1 to10 carbon atoms, a monovalent group having a group represented by—OCOX₃, where X₃ represents a monovalent hydrocarbon group having 1 to10 carbon atoms, a monovalent group having a group represented by—NX₄X₅, where X₄ and X₅ each, independently represent monovalenthydrocarbon groups having 1 to 10 carbon atoms, a monovalent grouphaving a group represented by —CONX₆X₇, where X₆ and X₇ each,independently represent monovalent hydrocarbon groups having 1 to 10carbon atoms, or a monovalent group containing a hydroxyl group. Forthis reason, these compounds have excellent polymerization property andphotocurability with less odor and low viscosity. Accordingly, suchcompounds represented by chemical formula 1, 2, 3, or 4 are suitable foruse in ink.

Since its intermolecular interaction is strong, an acrylamide having acarbonyl imino group has little odor but high viscosity, therebybecoming solid in some cases. For this reason, such an acrylamide is notsuitable for use in ink.

An acrylamide which has no carbonyl imino group and a polar group notbonded with a nitrogen bond has high volatility and significant odor.For this reason, such an acrylamide is not suitable for use in ink.

An acrylamide having a ring structure in its molecule is preferable. Insuch an acrylamide, hardness is imparted to a photopolymerized materialthereof, resulting in improvement of photocurability.

There is no specific limit to such a ring structure. Specific examplesthereof include, but are not limited to, an aliphatic ring, aheterocyclic ring, and an aromatic ring. Of these, a heterocyclic ringis preferable, a ring containing a nitrogen atom is more preferable, andthe ring A and the ring B are particularly preferable.

If a heterocyclic ring is introduced into the molecule of an acrylamide,the distance between molecules during polymerization becomes short dueto polarization caused by the presence of the hetero atoms, whichpromotes photopolymerization. In addition, in terms of interactionbetween molecules, if a ring containing hetero atoms is introduced intothe molecule of an acrylamide, hardness after photopolymerization isconsidered to become excellent.

An acrylamide having an oxy group or a carbonyl oxy group is preferable.An acrylamide having a carbonyl oxy group is more preferable. By havinga such a structure, photocurability is further improved.

In the compound represented by chemical formula 1, there is no specificlimit to R₁, X₁, X₂, X₃, X₄, X₅, X₆, and X₇. Specific examples thereofinclude, but are not limited to, a methyl group, an ethyl group, ann-propyl group, an isopropyl group, a t-butyl group, an n-pentyl group,an n-hexyl group, a cyclohexyl group, a phenyl group, and a benzylgroup.

R₁ is preferably a cycloalkyl group, an aryl group, or an aralkyl group.If R₁ is such a group, photocurability is improved.

R₂ is preferably a 2-hydroxyethyl group (—CH₂CH₂OH) or a grouprepresented by the following chemical formula 5.

The viscosity of the compound represented by chemical formula 1 isfurther decreased by using such a group.

In the compound represented by chemical formula 2, X₁, X₂, X₃, X₄, X₅,X₆, and X₇ are the same as above.

R₃ and R₄ are preferably 2-hydroxyethyl groups or groups represented bychemical formula 5, independently. The viscosity of the compoundrepresented by chemical formula 2 is further decreased by having such agroup.

In the compound represented by chemical formula 3, X₁, X₂, X₃, X₄, X₅,X₆, and X₇ are the same as above.

A preferable compound represented by chemical formula 3 is representedby the following chemical formula 6.

If such a compound is used as the compound represented by chemicalformula 3, photocurability and photopolymerization properties arefurther improved.

R₅ is preferably a group represented by —COOX₂, where X₂ represents ahydrocarbon group having 1 to 10 carbon atoms and more preferably anethyloxy carbonyl group (—COOCH₂CH₃). If R₅ is such a group,photocurability and photopolymerization properties are further improved.

In the compound represented by chemical formula 4, X₁, X₂, X₃, X₄, X₅,X₆, and X₇ are the same as above.

There is no specific limit to the hydrocarbon group having 1 to 10carbon atoms as R₅. Specific examples thereof include, but are notlimited to, a methyl group, an ethyl group, an n-propyl group, anisopropyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, acyclohexyl group, a phenyl group, and a benzyl group.

In the compound represented by chemical formula 1, there is no specificlimit to the compound having a monovalent group containing a grouprepresented by —OX₁ (where X₁ represents a monovalent hydrocarbon grouphaving 1 to 10 carbon atoms) as R₂. Specific examples thereof include,but are not limited to, compounds represented by the following chemicalformulae (where n is an integer of from 1 to 4, multiple X₁s areindependent from each other).

In the compound represented by chemical formula 2, there is no specificlimit to the compound independently having monovalent groups containinggroups represented by —OX₁ (where X₁ represents a monovalent hydrocarbongroup having 1 to 10 carbon atoms) as R₃ and R₄. Specific examplesthereof include, but are not limited to, compounds represented by thefollowing chemical formulae (where n and m each, independently representintegers of from 1 to 4, multiple X₁s are independent from each other).

In the compound represented by chemical formula 1, there is no specificlimit to the compound having a monovalent group containing a hydroxylgroup as R₂. Specific examples thereof include, but are not limited to,compounds represented by the following chemical formulae (where n is aninteger of from 1 to 4).

In the compound represented by chemical formula 2, there is no specificlimit to the compound independently having monovalent groups containinghydroxyl groups as R₃ and R₄. Specific examples thereof include, but arenot limited to, compounds represented by the following chemical formulae(where n and m each, independently represent integers of from 1 to 4).

In the compound represented by chemical formula 1, there is no specificlimit to the compound having a monovalent group containing a grouprepresented by —COOX₂ (where X₂ represents a monovalent hydrocarbongroup having 1 to 10 carbon atoms) as R₂. Specific examples thereofinclude, but are not limited to, compounds represented by the followingchemical formulae.

In the compound represented by chemical formula 2, there is no specificlimit to the compound independently having monovalent groups containinggroups represented by —COOX₂ (where X₂ represents a monovalenthydrocarbon group having 1 to 10 carbon atoms) as R₃ and R₄. Specificexamples thereof include, but are not limited to, compounds representedby the following chemical formulae (where multiple X₂s are independentfrom each other).

In the compound represented by chemical formula 1, there is no specificlimit to the compound having a monovalent group containing a grouprepresented by —OCOX₃ (where X₃ represents a monovalent hydrocarbongroup having 1 to 10 carbon atoms) as R₂. Specific examples thereofinclude, but are not limited to, compounds represented by the followingchemical formulae (where n is an integer of from 1 to 4, multiple X₃sare independent from each other).

In the compound represented by chemical formula 2, there is no specificlimit to the compound independently having monovalent groups containinggroups represented by —OCOX₃ (where X₃ represents a monovalenthydrocarbon group having 1 to 10 carbon atoms) as R₃ and R₄. Specificexamples thereof include, but are not limited to, compounds representedby the following chemical formulae (where n and m each, independentlyrepresent integers of from 1 to 4, multiple X₃s are independent fromeach other).

In the compound represented by chemical formula 1, there is no specificlimit to the compound independently having monovalent groups containinggroups represented by —NX₄X₅ (where X₄ and X₅ each, independentlyrepresent monovalent hydrocarbon groups having 1 to 10 carbon atoms) asR₂. Specific examples thereof include, but are not limited to, compoundsrepresented by the following chemical formulae.

In the compound represented by chemical formula 2, there is no specificlimit to the compound independently having monovalent groups containinggroups represented by —NX₄X₅ (where X₄ and X₅ represent monovalenthydrocarbon groups having 1 to 10 carbon atoms) as R₃ and R₄. Specificexamples thereof include, but are not limited to, compounds representedby the following chemical formulae (where multiple X₄s and X₅s each, areindependent from each other).

In the compound represented by chemical formula 1, there is no specificlimit to the compound independently having monovalent groups containinggroups represented by —CONX₆X₇ (where X₆ and X₇ each, independentlyrepresent monovalent hydrocarbon groups having 1 to 10 carbon atoms) asR₂. Specific examples thereof include, but are not limited to, compoundsrepresented by the following chemical formulae.

In the compound represented by chemical formula 2, there is no specificlimit to the compound independently having monovalent groups containinggroups represented by —CONX₆X₇ (where X₆ and X₇ each, independentlyrepresent monovalent hydrocarbon groups having 1 to 10 carbon atoms) asR₃ and R₄. Specific examples thereof include, but are not limited to,compounds represented by the following chemical formulae (where multipleX₆s and X₇s each, are independent from each other).

In the compound represented by chemical formula 3, there is no specificlimit to the compound independently having monovalent groups containinggroups represented by —NX₄X₅ (where X₄ and X₅ each, independentlyrepresent monovalent hydrocarbon groups having 1 to 10 carbon atoms) asR₅. Specific examples thereof include, but are not limited to, compoundsrepresented by the following chemical formulae (where m represents 0 oran integer of from 1 to 6).

In the compound represented by chemical formula 3, there is no specificlimit to the compound having a monovalent group containing a grouprepresented by —OX₁ (where X₁ represents a monovalent hydrocarbon grouphaving 1 to 10 carbon atoms) as R₅. Specific examples thereof include,but are not limited to, compounds represented by the following chemicalformulae (where Y is a hydrogen atom or a methyl group, n is an integerof from 1 to 4, and m represents 0 or an integer of from 1 to 6).

In the compound represented by chemical formula 3, there is no specificlimit to the compound having a monovalent group containing a grouprepresented by —COOX₂ (where X₂ represents a monovalent hydrocarbongroup having 1 to 10 carbon atoms) as R₅. Specific examples thereofinclude, but are not limited to, compounds represented by the followingchemical formulae (where m represents 0 or an integer of from 1 to 6).

In the compound represented by chemical formula 3, there is no specificlimit to the compound having a monovalent group containing a grouprepresented by —OCOX₃ (where X₃ represents a monovalent hydrocarbongroup having 1 to 10 carbon atoms) as R₅. Specific examples thereofinclude, but are not limited to, compounds represented by the followingchemical formulae (where Y is a hydrogen atom or a methyl group, n is aninteger of from 1 to 4, and m represents 0 or an integer of from 1 to6).

In the compound represented by chemical formula 4, there is no specificlimit to the compound having an alkyl group having 1 to 10 carbon atomsas R₆. Specific examples thereof include, but are not limited to,compounds represented by the following chemical formulae (where mrepresents 0 or an integer of from 1 to 6).

In the compound represented by chemical formula 4, there is no specificlimit to the compound independently having monovalent groups containinggroups represented by —NX₄X₅ (where X₄ and X₅ each, independentlyrepresent monovalent hydrocarbon groups having 1 to 10 carbon atoms) asR₆. Specific examples thereof include, but are not limited to, compoundsrepresented by the following chemical formulae (where m represents 0 oran integer of from 1 to 6).

In the compound represented by chemical formula 4, there is no specificlimit to the compound having a monovalent group containing a grouprepresented by —OX₁ (where X₁ represents a monovalent hydrocarbon grouphaving 1 to 10 carbon atoms) as R₆. Specific examples thereof include,but are not limited to, compounds represented by the following chemicalformulae (where Y is a hydrogen atom or a methyl group, n is an integerof from 1 to 4, and m represents 0 or an integer of from 1 to 6).

In the compound represented by chemical formula 4, there is no specificlimit to the compound having a monovalent group containing a grouprepresented by —COOX₂ (where X₂ represents a monovalent hydrocarbongroup having 1 to 10 carbon atoms) as R₆. Specific examples thereofinclude, but are not limited to, compounds represented by the followingchemical formulae (where m represents 0 or an integer of from 1 to 6).

In the compound represented by chemical formula 4, there is no specificlimit to the compound having a monovalent group containing a grouprepresented by —OCOX₃ (where X₃ represents a monovalent hydrocarbongroup having 1 to 10 carbon atoms) as R₆. Specific examples thereofinclude, but are not limited to, compounds represented by the followingchemical formulae (where Y is a hydrogen atom or a methyl group, n is aninteger of from 1 to 4, and m represents 0 or an integer of from 1 to6).

The compound represented by chemical formula 1, 2, 3, or 4 has aviscosity of 100 mPa·s or less at 25° C. and, preferably, 50 mPa·s orless.

The ink of the present disclosure may contain two or more kinds of thecompounds represented by chemical formula 1, 2, 3, or 4.

The total content of the compound represented by chemical formula 1, 2,3, or 4 in the ink ranges from 20% by weight to 98% by weight,preferably from 30% by weight to 90% by weight, and more preferably from30% by weight to 80% by weight.

It is preferable that the ink contains a photopolymerization initiator.

Specific examples of the photopolymerization initiator include, but arenot limited to, a photoradical polymerization initiator, a photocationpolymerization initiator (photoacid producing agent), and a photoanionpolymerization initiator (photobase producing agent). These can be usedalone or in combination. Of these, photoradical polymerizationinitiators and photoanion polymerization initiators are preferable.

The photopolymerization initiator is a compound producing apolymerization initiating species by absorbing an active energy ray.

There is no specific limit to the active energy ray. Specific examplesthereof include, but are not limited to, gamma ray, beta ray, anelectron beam, an ultraviolet ray, visible light, and an infrared ray.

There is no specific limit to the photopolymerization initiator.Specific examples thereof include, but are not limited to, aromaticketones, acyl phosphine oxide compounds, aromatic onium salt compounds,organic peroxides, thio compounds, hexaaryl biimidazol compounds,ketoxim ester compounds, borate compounds, adinium compounds,metallocene compounds, active ester compounds, compounds having carbonhalogen bonds, and alkyl amine compounds.

Specific examples of photoradical polymerization initiators include, butare not limited to, benzophenone, Michler's ketone,4,4′-bis(diethylamino)benzophenone, xanthone, thioxanthone, isopropylxanthone, 2,4-diethylthio xanthone, 2-ethyl anthraquinone, acetophenone,2-hydroxy-2-methyl propiophenone, 2-hydroxy-2-methyl-4′-isopropylpropiophenone, 1-hydroxy cyclohexyl phenyl keton, isopropyl benzoinether, isobutyl benzoin ether, 2,2-diethoxy acetophenone,2,2-dimethoxy-2-phenylacetophenone, Camphorquinone, benzanthrone,2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropane-1-one,2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butanone-1,4-dimethylaminoethyl benzoate, 4-dimethylamino isoamyl benzoate,4,4′-bis(t-butylperoxycarbonyl)benzophenone,3,4,4′-tris(t-butylperoxycarbonyl)benzophenone,3,3′,4,4′-tetra(t-butylperoxycarbonyl)benzophenone,3,3′,4,4′-tetra(t-hexylperoxycarbonyl)benzophenone,3,3′-bis(methoxycarbonyl)-4,4′-bis(t-butylperoxycarbonyl)benzophenone,3,4′-bis(methoxycarbonyl)-4,3′-bis(t-butylperoxycarbonyl)benzophenone,4,4′-bis(methoxycarbonyl)-3,3′-bis(t-butylperoxycarbonyl)benzophenone,1,2-octane dione, 1-[4-(phenylthio)phenyl]-2-(o-benzoyloxime),2-(4′-methoxystyryl)-4,6-bis(trichloromethyl)-s-triadine,2-(3′,4′-dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triadine,2-(2′,4′-dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triadine,2-(2′-methoxystyryl)-4,6-bis(trichloromethyl)-s-triadine,2-(4′-pentyloxystyryl)-4,6-bis(trichloromethyl)-s-triadine,4-[p-N,N-bis(ethoxycarbonylmethyl)-2,6-bis(trichloromethyl)-s-triadine,1,3-bis(trichloromethyl)-5-(2′-chlorophenyl)-s-triadine,1,3-bis(trichloromethyl)-5-(4′-methoxyphenyl)-s-triadine,2-(p-dimethylaminostyryl)benzoxazole,2-(p-dimethylaminostyryl)benzthiazole, 2-mercaptobenzthiazole,3,3′-carbonylbis(7-diethylamino coumarin),2-(o-chlorophenyl)-4,4′,5,5′-tetraphenyl-1,2′-biimidazole,2,2′-bis(2-chlorophenyl)-4,4′,5,5′-tetrakis(4-ethoxycarbonylphenyl)-1,2′-biimidazole,2,2′-bis(2,4-dichlorophenyl)-4,4′,5,5′-tetraphenyl-1,2′-biimidazole,2,2′-bis(2,4-dibromophenyl)-4,4′,5,5′-tetraphenyl-1,2′-biimidazole,2,2′-bis(2,4,6-trichlorophenyl)-4,4′,5,5′-tetraphenyl-1,2′-biimidazole,3-(2-methyl-2-dimethylaminopropionyl)carbazole,3,6-bis(2-methyl-2-morpholinopropionyl)-9-n-dodecyl carbazole, 1-hydroxycyclohexyl phenylketone,bis(η5-2,4-cyclopentadiene-1-yl)-bis[2,6-difluoro-3-(1-H-pyrrol-1-yl)phenyl]titanium,bis(2,4,6-trimethylbenzoyl)phenyl phosphine oxide, and2,4,6-trimethylbenzoyl)diphenyl phosphine oxide.

Of these, bis(2,4,6-trimethylbenzoyl)phenyl phosphine oxide (IRGACURE819, manufactured by BASF Japan), 2,4,6-trimethylbenzoyl)diphenylphosphine oxide (DAROCUR TPO, manufactured by BASF Japan),1-hydroxycylohexyl phenyl ketone (IRGACURE 184, manufactured by BASFJapan), 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropane-1-one(IRGACURE 907, manufactured by BASF Japan), and2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholine-4-ylphenyl)butane-1-one(IRGACURE 379, manufactured by BASF Japan) are preferable because theseare highly soluble in other components contained in ink and the ink canbe cured by exposure to a small amount of ultraviolet ray.

The mass ratio of the photopolymerization initiator to the total amountof the compound represented by chemical formula 1, 2, 3, or 4 and thecoloring agent ranges from 0.01 to 0.50, preferably from 0.02 to 0.40,and more preferably from 0.05 to 0.30.

The ink of the present disclosure optionally contains a coloring agent.By the coloring agent, a colored image can be formed.

There is no specific limit to the coloring agent. Specific examples ofthe coloring agent include, but are not limited to, pigments,oil-soluble dyes, hydrosoluble dyes, and disperse dyes. These can beused alone or in combination.

Of these, pigments and oil-soluble dyes are preferable and of the two,pigments are more preferable because these are tough to environmentchange.

It is preferable that the coloring agent does not serve aspolymerization inhibitor in order not to have an adverse impact on thesensitivity of photopolymerization reaction by active energy ray.

Specific examples of red pigments or magenta pigments include, but arenot limited to, Pigment Red 3, 5, 19, 22, 31, 38, 43, 48:1, 48:2, 48:3,48:4, 48:5, 49:1, 53:1, 57:1, 57:2, 58:4, 63:1, 81, 81:1, 81:2, 81:3,81:4, 88, 104, 108, 112, 122, 123, 144, 146, 149, 166, 168, 169, 170,177, 178, 179, 184, 185, 208, 216, 226, and 257, Pigment Violet 3, 19,23, 29, 30, 37, 50, and 88, and Pigment Orange 13, 16, 20, and 36.

Specific examples of blue pigments or cyan pigments include, but are notlimited to, Pigment Blue 1, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 17-1,22, 27, 28, 29, 36, and 60.

Specific examples of green pigments include, but are not limited to,Pigment Green 7, 26, 36, and 50.

Specific examples of yellow pigments include, but are not limited to,Pigment Yellow 1, 3, 12, 13, 14, 17, 34, 35, 37, 55, 74, 81, 83, 93, 94,95, 97, 108, 109, 110, 137, 138, 139, 153, 154, 155, 157, 166, 167, 168,180, 185, and 193.

Specific examples of black pigments include, but are not limited to,Pigment Black 7, 28, and 26.

Specific examples of white pigments include, but are not limited to,Pigment White 6, 18, and 21.

Specific examples of the oil-soluble yellow dyes include, but are notlimited to, an aryl or heteryl azo dye having a phenolic compound, anaphthol compound, an aniline compound, a pyrazolone compound, apyridone compound, or a compound having an open chain active methylenecompound as coupling component, a methine dye such as an azomethine, abenzylidene dye, or a monomethine oxonol having an open chain activemethylene compound as coupling component, a quinone dye such as anaphthoquinone dye and an anthraquinone dye, a quinophthalone dye, anitro⋅nitroso dye, an acrylidine dye, and an acrydinone dye.

Specific examples of the oil-soluble magenta dyes include, but are notlimited to, an aryl or heteryl azo dye having a phenolic compound, anaphthol compound, or an aniline compound as coupling component, amethine dye such as an azomethine dye, an arylidene dye, a styryl dye, amerocyanine dye, or an oxonol dye having a pyrazolone or a pyridone ascoupling component, a carbonium dye such as diphenyl methane dye, atriphenyl methane dye, and a xanthene dye, a quinone dye such as anaphthoquinone dye, an anthraquinone dye, and an anthrapyridone dye, anda condensed polycyclic dye such as a dioxadine dye.

Specific examples of the oil-soluble cyan dyes include, but are notlimited to, an indoaniline dye, an indophenol dye, a polymethine dyesuch as azomethine dye, cyanine dye, oxonol dye, and merocycnine dyehaving a pyrrolo triazole as coupling component, a carbonium dye such asdiphenyl methane dye, a triphenyl methane dye, and a xanthene dye, aphthalocyanine dye, an anthraquinone dye, an aryl or heteryl azo dyehaving a phenolic compound, a naphthol compound, or an aniline compoundas coupling component, and indigo⋅thioindigo dye.

Specific examples of the oil-soluble dyes include, but are not limitedto, C.I. Solvent Black 3, 7, 27, 29, and 34, C.I. Solvent Yellow 14, 16,19, 29, 30, 56, 82, 93, and 162, C.I. Solvent Red 1, 3, 8, 18, 24, 27,43, 49, 51, 72, 73, 109, 122, 132, and 218; C.I. Solvent Violet 3; C.I.Solvent Blue 2, 11, 25, 35, 38, 67, and 70; C.I. Solvent Green 3 and 7,and C.I. Solvent Orange 2.

Specific examples of the disperse dyes include, but are not limited to,C.I. Disperse Yellow 5, 42, 54, 64, 79, 82, 83, 93, 99, 100, 119, 122,124, 126, 160, 184:1, 186, 198, 199, 201, 204, 224, and 237 C.I.Disperse Orange 13, 29, 31:1, 33, 49, 54, 55, 66, 73, 118, 119, and 63;C.I. Disperse Red 54, 60, 72, 73, 86, 88, 91, 92, 93, 111, 126, 127,134, 135, 143, 145, 152, 153, 154, 159, 164, 167:1, 177, 181, 204, 206,207, 221, 239, 240, 258, 277, 278, 283, 311, 323, 343, 348, 356, and362; C.I. Disperse Violet 33, C.I. Disperse Blue, 60, 73, 87, 113, 128,143, 148, 154, 158, 165, 165:1, 165:2, 176, 183, 185, 197, 198, 201,214, 224, 225, 257, 266, 267, 287, 354, 358, 365, and 368, and C.I.Disperse Green 6:1 and 9.

It is preferable that such pigments is moderately dispersed in ink

There is no specific limit to a dispersion device to disperse a pigment.Specific examples thereof include, but are not limited to, a ball mill,a sand mill, a ring mill, an attritor, a roll mill, an aditator, aHENSCHEL MIXER, a colloid mill, an ultrasonic homogenizer, a pearl mill,a wet-type jet mill, and a paint shaker.

It is possible to add a dispersing agent when dispersing a pigment.

There is no specific limit to such a dispersing agent. A polymerdispersing agent is preferable.

The mass ratio of a dispersing agent to a pigment ranges from 0.01 to0.50.

The average particle diameter of the pigment in ink ranges from 0.005 μmto 0.5 μm, preferably from 0.01 μm to 0.45 μm, and more preferably from0.015 μm to 0.4 μm.

When the average particle diameter is within such a range, it ispossible to suppress clogging of the nozzle of an ink jet head andmaintain the preservation stability, the transparency, and thephotocurability of ink.

The content of the coloring agent in ink ranges from 0.5% by weight to10% by weight and preferably from 1% by weight to 8% by weight.

The content of the coloring agent in white ink having a white pigmentformed of titanium oxide as coloring agent ranges from 5% by weight to30% by weight and preferably from 10% by weight to 25% by weight. Whenthe content is within such a range, it is possible to maintain theshielding property of ink.

The ink of the present disclosure may include a photopolymerizablecompound other than the compound represented by chemical formula 1, 2,3, or 4.

The mass ratio of the photopolymerizable compound other than thecompound represented by chemical formula 1, 2, 3, or 4 to the compoundrepresented by chemical formula 1, 2, 3, or 4 ranges from 0.01 to 100and preferably from 0.1 to 50.

There is no specific limit to the photopolymerizable compound other thanthe compound represented by chemical formula 1, 2, 3, or 4. Specificexamples thereof include, but are not limited to, a photoradicalpolymerizable compound, a photocation polymerizable compound, aphotoanion polymerizable compound. These can be used alone or incombination.

As the photoradical polymerizable compound, any compound that has atleast one ethylene-based unsaturated group capable of photoradicalpolymerization is suitable for use. These include, monomers, oligomers,polymers, etc.

The photoradical polymerizable compound include, but are not limited to,unsaturated carboxylic acids such as acrylic acid, methacrylic acid,itaconic acid, crotonic acid, isocrotonic acid, and maleic acid, saltsthereof, and compounds derived therefrom, anhydrides havingethylene-based unsaturated groups, acrylonitrile, styrene, unsaturatedpolyesters, unsaturated polyethers, unsaturated polyamides, andunsaturated urethanes.

Specific examples of the photoradical polymerizable compound include,but are not limited to derivatives of acrylic acid such as2-hydroxyethyl acrylate, butoxyethyl acrylate, carbitol acrylate,cyclohecyl acrylate, tetrahydrofurfuryl acrylate, benzyl acrylate,bis(4-acryloxy polyethoxyphenyl)propane, neopentyl glycol diacrylate,ethoxified neopentyl glycol diacrylate, propoxynated neopentyl glycoldiacrylate, 1,6-hexane diol diacrylate, ethylene glycol diacrylate,diethylene glycol diacrylate, triethylene glycol diacrylate,tetraethylene glycol diacrylate, polyethylene glycol diacrylate,propylene glycol diacrylate, dipropylene glycol diacrylate, tripropyleneglycol diacrylate, tetrapylene glycol diacrylate, polypropylene glycoldiacrylate, pentaerythriol triacrylate, pentaerythriol tetraacrylate,dipentaerythriol tetraacrylate, trimethylol propane triacrylate,tetramethylol methane tetraacrylate, oligoester acrylate, andepoxyacrylate; derivatives of methacrylic acid such as methylmethacrylate, n-butyl methacrylate, allyl methacrylate, glycidylmethacrylate, benzyl methacrylate, dimethylaminomethyl methacrylate,1,6-hexane diol dimethacrylate, ethylene glycol dimethacrylate,triethylene glycol dimethacrylate, polyethylene glycol dimethacrylate,polypropylene glycol dimethacrylate, trimethylol ethane trimethacrylate,trimethytlol propane trimethacrylate, and 2,2-bis(4-methacryloxypolyethoxy phenyl)propane; derivatives of acrylic amide such asN-methylol acrylic amide, diacetone acrylic amide, 2-hydroxyethylacrylic amide, and acryloyl morpholine; derivatives of allyl compoundssuch as allyl glycidyl ether, diallyl phthalate, and triallyltrimellitate, di- or tri-vinyl ether compounds such as ethylene glycoldivinyl ether, ethylene glycol monovinyl ether, diethylene glycoldivinyl ether, triethylene glycol monovinyl ether, triethylene glycoldivinyl ether, propylene glycol divinyl ether, dipropylene glycoldivinyl ether, butane diol divinyl ether, hexane diol divinyl ether,cyclohexane dimethanol divinyl ether, hydroxyethyl monovinyl ether,hydroxynonyl monovinyl ether, and trimethylol propane trivinyl ether;monovinylether compounds such as ethylvinylether, n-butylvinylether,isobutylvinylether, octadecylvinylether, cyclohexylvinylether,hydroxybutylvinylether, 2-ethylhexylvinylether, cyclohexanedimethanolmonovinylether, n-propyl vinylether, idopropyl vinylether, isopropenylether-o-propylene carbonate, dodecyl vinylether, diethylene glycolmonovinylether, and octadecylvinylether; 2-ethylhexyl diglycol acrylate,2-hydroxy-3-phenoxypropyl acrylate, 2-hydroxybutylacrylate, hydroxypivalic acid neopentyl glycol diacrylate, 2-acryloyloxy ethyl phthalicacid, methoxy polyethylene glycol acrylate, tetramethylol methanetriacrylate, 2-acryloyloxy ethyl-2-hydroxy ethyl phthalic acid,dimethylol tricyclodecane diacrylate, ethoxified phenyl acrylate,2-acryloyloxy ethyl succinic acid, an acrylate of an adduct of nonylphenol with ethylene oxide, a modified glycerine acrylate, an adduct ofbisphenol A with diglycidyl ether acrylic acid, a modified bisphenol Adiacrylate, a phenoxypolyethylene glycol acrylate, 2-acryloyloxyethylhexahydrophthalic acid, a diacrylate of an adduct of bisphenol A withpropylene oxide, a diacrylate of an adduct of bisphenol A with ethyleneoxide, dipentaerythritol hexaacrylate, pentaerythritol triacrylate,tolylene diisocyanate urethane prepolymer, lactone-modified flexibleacrylate, buthoxyethyl acrylate, an adduct of propylene glycol withdiglycidyl ether acrylic acid, pentaerythritol triacrylate,hexamethylene diisocyanate urethane prepolymer, 2-hydroxyethyl acrylate,methoxy dipropylene glycol acrylate, ditrimethylol propanetetraacrylate, pentaerythritol triacrylate, hexamethylene diisocyanateurethane prepolymer, stearyl acrylate, isoamylacrylate, isomyristylacrylate, isostearyl acrylate, and lactone-modified acrylate.

As the combination of the photopolymerizable compound and thephotopolymerization initiator, in addition to the combination of thephotoradical polymerizable compound and the photoradical polymerizationinitiator, a combinational use of a photocation polymerizable compoundand a photocation polymerization initiator and a combinational use of aphotoanion photopolymerizable compound and a photoanion polymerizationinitiator are also suitable.

Specific examples of the photocation polymerizable compounds include,but are not limited to, epoxy compounds, vinylether compounds, andoxetane compounds.

Specific examples of the photocation polymerization initiator include,but are not limited to, salts of B(C₆F₅)₄ ⁻, PF₅ ⁻, ASF₆ ⁻, SbF₆ ⁻, andCF₃SO₃ ⁻ of aromatic onium compounds of diazonium, ammonium, iodonium,sulphonium, and phosphonium, sulphone compounds capable of producingsulfonic acid, halogenated compounds capable of producing halogenatedhydrogen, and iron allene complexes.

Specific examples of the photoanion polymerizable compounds include, butare not limited to, epoxy compounds, lactone compounds, acryliccompounds, and methacrylic compounds. Of these, the acrylic compoundsand methacrylic compounds specified as preferable photoradicalpolymerizable compounds are preferable.

Specific examples of photoanion polymerization initiator include, butare not limited to, o-nitrobenzyl carbamate derivatives, o-acyloxyderivatives, and o-carbamoyloxime amidine.

The ink of the present disclosure optionally contains a sensitizer topromote decomposition of a photopolymerization initiator upon exposureto active energy ray.

A sensitizer is excited by absorbing active energy ray. When thesensitizer in the excited state contacts a polymerization initiator,chemical change of the polymerization initiator is promoted by electrontransfer, energy transfer, heat, etc.

There is no specific limit to the sensitizer. For example, a sensitizingpigment having an absorption wavelength in a range of from 350 nm to 450nm is suitable.

Specific examples of the sensitizing pigment having an absorptionwavelength in a range of from 350 nm to 450 nm include, but are notlimited to, multi-nuclear aromatic compounds (such as pyrene, perylene,and triphenylene), xanthenes (such as flourescein, eosin, Erythrosin,Rhodamine B, and rose bengal), cyanines (such as thiacarbocyanine andoxacarbocyanine), merocyanines (such as merocyanine andcarbomerocyanine), thiazines (such as thionine, methylene blue, andtoluidine blue), acridines (such as acridine orange, chloroflavin, andacriflavin), anthraquinones (such as anthraquinone), squarylium (such assquarylium), and coumalins (such as 7-diethylamino-4-methyl coumalin).

The mass ratio of this sensitizing pigment to a photopolymerizationinitiator ranges from 5×10⁻³ to 200 and preferably from 0.02 to 50.

The link of the present disclosure optionally contains a co-sensitizer.

Co-sensitizers enhances the sensitivity of sensitizing pigments toactive energy ray or subdues polymerization inhibition ofphotopolymerizable compounds by oxygen.

There is no specific limit to such co-sensitizers. Specific examplesthereof include, but are not limited to, amine-based compounds such astriethanol amines, p-dimethyl amino benzoic acid ethyl esters, p-formyldimethylaniline and p-methylthio dimethylaniline, thiols such as2-mercapto benzothiazole, 2-mercaptobenzooxazole, 2-mercaptobenzoimidazole, 2-mercapto-4(3H)-quinazoline, and β-mercaptonaphthalene, and sulfides.

The ink of the present disclosure may contain a polymerizationinhibitor. The preservation stability of ink is improved by apolymerization inhibitor. In addition, it is possible to preventclogging of the nozzle of an ink jet head due to thermal polymerizationwhen ink is heated to decrease the viscosity thereof before discharging.

There is no specific limit to the polymerization inhibitor. Specificexamples thereof include, but are not limited to, hydroquinone,benzoquinone, p-methoxyphenol, TEMPO, TEMPOL, and a cupferron complex ofaluminum.

The content of a polymerization inhibitor in ink ranges from 200 ppm to20,000 ppm

The viscosity of ink ranges from 7 mPa·s to 30 mPa·s and preferably from7 mPa·s to 25 mPa·s taking into account the discharging properties ofthe ink in an ink jet device.

Since the ink of the present disclosure is of an active energy raycuring type, it is preferable that it does not contain a solvent.However, to improve the attachability between the ink after curing and arecording medium, it may further contain a solvent more unless thecuring speed of the ink is not affected.

There is no specific limit to the selection of solvent. Examples thereofare, organic solvents and water.

The content of an organic solvent in ink is from 0.1% by weight to 5% byweight and preferably from 0.1% by weight to 3% by weight.

Furthermore, the ink optionally contains a surfactant, a levelingadditive, a matte agent, and resins such as polyester resins,polyurethane resins, vinyl resins, acrylic resins, rubber resins, andwax resins to adjust film properties.

In addition, the ink optionally contains a tackifier having nopolymerization inhibition effect to improve the attachability of the inkto polyolefin, PET, etc.

The ink of the present disclosure can be accommodated in a container inan ink cartridge. If ink is used in an ink cartridge, a user does nottouch the ink directly in operations such as ink replacement, therebyavoiding contamination of hands, fingers and clothes. Also, it ispossible to prevent mingling of foreign objects such as rubbish intoink.

There is no specific limit to the selection of the container, forexample, ink bags formed of materials with no air permeability such asaluminum laminate film or resin film are suitable.

FIG. 1 is a diagram illustrating an example of the ink cartridgeaccording to an embodiment of the present invention.

An ink bag 11 has an ink inlet 12 and an ink outlet 13. The ink bag 11is filled with ink through the ink inlet 12. Subsequent to evacuation ofair remaining in the ink bag 11, the ink inlet 12 is sealed by fusion.When using the ink bag 11, the ink outlet 13 is pierced with a needleformed on an ink jet recording device to supply the ink to the ink jetrecording device. The ink outlet 13 is formed of a rubber material.

The ink bag 11 is accommodated in a cartridge housing 14 made ofplastic, which is detachably attached to the ink jet recording device asthe ink cartridge 10. Since the ink cartridge 10 is detachablyattachable to the ink jet recording device, it is possible to improvethe working efficiency of supplement or replacement of ink.

The ink jet recording device of the present disclosure has the inkcartridge and an ink discharging head to discharge ink for recording.

There is no specific limit to the ink discharging method, for example, acontinuous spraying method and an on-demand method are useful.

The on-demand method employs a piezo system, a thermal system, or anelectrostatic system.

The printing mechanism of the ink jet recording device is described withreference to FIG. 2.

Due to printing units 23 a, 23 b, 23 c, and 23 d of colors of yellow,magenta, cyan, and black, ink is discharged to a print substrate 22 fedfrom a print substrate supplying roll 21. The ink is separatelydischarged per color of yellow, magenta, cyan, and black. Thereafter,the ink is exposed to ultraviolet ray emitted from light sources 24 a,24 b, 24 c, and 24 d to photocure the ink, so that a color image isformed. Thereafter, the print substrate 22 is transferred to a processunit 25 and a printed matter roll-up roll 26.

A heating unit is optionally provided to each of the printing units 23a, 23 b, 23 c, and 23 d at the ink discharging portion to liquidize ink.

The temperature of the print substrate may rise when the printed area ofthe previous color is large or the transfer speed of the print substrateis high. For this reason, a mechanism of cooling down a print substrateto around room temperature is provided in a contact or non-contactmanner as an option.

There is no specific limit to the print substrate 22, typically paper,film, metal, or mixtures thereof.

The print substrate 22 may have a sheet-like form.

In addition, it is possible to have an installation for simplex printingand duplex printing.

Furthermore, it is possible to irradiate the print substrate withultraviolet ray emitted from the light source 24 d while exposure toultraviolet ray from the light sources 24 a, 24 b, and 24 c is weakenedor omitted. This contributes to energy-saving and cost efficiency.

A composition that contains the compound represented by chemical formula1, 2, 3, or 4 can be used as adhesive or applicable to form solidobjects.

Having generally described preferred embodiments of this invention,further understanding can be obtained by reference to certain specificexamples which are provided herein for the purpose of illustration onlyand are not intended to be limiting. In the descriptions in thefollowing examples, the numbers represent weight ratios in parts, unlessotherwise specified.

EXAMPLES

Next, the present disclosure is described in detail with reference toExamples and Comparative examples but not limited thereto.

¹H-NMR spectrum was monitored by using a ¹H-NMR (500 MHz) (manufacturedby JEOL Ltd.). FT-IR Spectrum GX (manufactured by PerkinElmer Co., Ltd.)was used for IR spectrum. Mass spectrum was monitored by LCT Premer XE(manufactured by MICROMASS TECHNOLOGIES).

Example 1

8.0 g (90 mmol) of N-2-(methoxyethyl)methyl amine was added to 100 ml ofdehydrated dichlormethane in a flask followed by Ar gas replacement.Thereafter, 13.4 g (132 mmol) of triethyl amine was added thereto. Next,the system was cooled down to about −10° C. 10.0 g (110 mmol) of acrylicacid chloride was slowly dropped in the system while keeping thetemperature in the system ranged from −10° C. to −5° C. and thereafterstirred for two hours at room temperature. Furthermore, subsequent toremoval of precipitants by filtration, the filtrate was washed withsaturated sodium hydrogen carbonate aqueous solution and saturatedsodium chloride aqueous solution. Next, subsequent to drying by sodiumsulfate, the dried resultant was condensed under a reduced pressure toobtain an oily brown material. Furthermore, by a column chromatographyfilled with 300 g of Wakogel C300 (manufactured by Wako Pure ChemicalIndustries, Ltd.) using hexane and ethyl acetate as eluate, the oilybrown material was fined to obtain 5.8 g (yield: about 45%) of an oily,pale yellow material represented by the following chemical formula.

¹H-NMR(CDCl₃):δ3.04(s,1.5H),3.15(s,1.5H),3.35(s,3H)3.49-3.64(m,4H)5.63-5.71(m,1H),6.28-6.35(m,1H),6.56-6.66(m,1H)

IR(NaCl):2982,2932,2892,2830,1651,1613,1450,1417,1404,1359,1282,1192,1117,1060,1018,982,958,826,795,747,607,536cm⁻¹

Example 2

8.0 g (60 mmol) of bis(methoxyethyl) amine was added to 100 ml ofdehydrated dichlormethane in a flask followed by Ar gas replacement.Thereafter, 8.8 g (87 mmol) of triethyl amine was added thereto. Next,the system was cooled down to about −10° C. 6.5 g (72 mmol) of acrylicacid chloride was slowly dropped in the system while keeping thetemperature in the system ranged from −10° C. to −5° C. and thereafterstirred for two hours at room temperature. Furthermore, subsequent toremoval of precipitants by filtration, the filtrate was washed withsaturated sodium hydrogen carbonate aqueous solution and saturatedsodium chloride aqueous solution. Next, subsequent to drying by sodiumsulfate, the dried resultant was condensed under a reduced pressure toobtain an oily brown material.

Furthermore, by a column chromatography filled with 300 g of WakogelC300 (manufactured by Wako Pure Chemical Industries, Ltd.) using hexaneand ethyl acetate as eluate, the oily brown material was fined to obtain5.5 g (yield: about 50%) of an oily, pale yellow material represented bythe following chemical formula.

¹H-NMR (CDCl₃):δ3.34(d,6H),3.51(t,2H),3.57(t,2H),3.63(t,4H),5.67(dd,1H),6.34(dd,1H),6.64-6.69(m,1H)

IR(NaCl):2982,2930,2981,2829,1651,1613,1447,1366,1315,1270,1230,1193,1157,1118,1069,1015,981,962,824,795,529cm⁻¹

Example 3

9.7 g (60 mmol) of bis(ethoxyethyl) amine was added to 100 ml ofdehydrated dichloromethane in a flask followed by Ar gas replacement.Thereafter, 8.8 g (87 mmol) of triethyl amine was added thereto. Next,the system was cooled down to about −10° C. 6.5 g (72 mmol) of acrylicacid chloride was slowly dropped in the system while keeping thetemperature in the system ranged from −10° C. to −5° C. and thereafterstirred for two hours at room temperature. Furthermore, subsequent toremoval of precipitants by filtration, the filtrate was washed withsaturated sodium hydrogen carbonate aqueous solution and saturatedsodium chloride aqueous solution. Next, subsequent to drying by sodiumsulfate, the dried resultant was condensed under a reduced pressure toobtain an oily brown material. Furthermore, by a column chromatographyfilled with 300 g of Wakogel C300 (manufactured by Wako Pure ChemicalIndustries, Ltd.) using hexane and ethyl acetate as eluate, 6.5 g(yield: about 50%) of an oily, pale yellow material represented by thefollowing chemical formula was obtained.

¹H-NMR(CDCl₃):δ1.18(t,6H),3.48(q,4H),3.55(t,2H),3.59-3.66(m,6H),5.67(dd,1H),6.33(dd,1H),6.65-6.72(m,1H)

IR(NaCl):2976,2933,2868,1651,1614,1471,1445,1373,1353,1317,1277,1225,1118,980,795,522cm⁻¹

Example 4

8.3 g (70 mmol) of methylamino acetoaldehyde dimethyl acetal was addedto 100 ml of dehydrated dichlormethane in a flask followed by Ar gasreplacement. Thereafter, 10.1 g (100 mmol) of triethyl amine was addedthereto. Next, the system was cooled down to about −10° C. 7.6 g (84mmol) of acrylic acid chloride was slowly dropped in the system whilekeeping the temperature in the system ranged from −10° C. to −5° C. andthereafter stirred for two hours at room temperature. Furthermore,subsequent to removal of precipitants by filtration, the filtrate waswashed with saturated sodium hydrogen carbonate aqueous solution andsaturated sodium chloride aqueous solution. Next, subsequent to dryingby sodium sulfate, the dried resultant was condensed under a reducedpressure to obtain an oily brown material. Furthermore, by a columnchromatography filled with 300 g of Wakogel C300 (manufactured by WakoPure Chemical Industries, Ltd.) using hexane and ethyl acetate aseluate, the oily brown material was fined to obtain 7.3 g (yield: about60%) of an oily, pale yellow material represented by the followingchemical formula.

¹H-NMR(CDCl₃):δ3.06(s,1H),3.15(s,2H),3.42(d,6H),3.50(dd,2H),4.42(t,0.35H),4.54(t,0.65H),5.64-5.74(m,1H),6.30-6.38(m,1H),6.57-6.69(m,1H)

IR(NaCl):2941,2835,1652,1614,1452,1417,1378,1308,1276,1240,1190,1123,1075,982,919,819,796,544cm⁻¹

Example 5

9.5 g (50 mmol) of imino diethyl diacetate was added to 100 ml ofdehydrated dichlormethane in a flask followed by Ar gas replacement.Thereafter, 7.3 g (72 mmol) of triethyl amine was added thereto. Next,the system was cooled down to about −10° C. 5.4 g (60 mmol) of acrylicacid chloride was slowly dropped in the system while keeping thetemperature in the system ranged from −10° C. to −5° C. and thereafterstirred for two hours at room temperature. Furthermore, subsequent toremoval of precipitants by filtration, the filtrate was washed withsaturated sodium hydrogen carbonate aqueous solution and saturatedsodium chloride aqueous solution. Next, subsequent to drying by sodiumsulfate, the dried resultant was condensed under a reduced pressure toobtain an oily brown material. Furthermore, by a column chromatographyfilled with 300 g of Wakogel C300 (manufactured by Wako Pure ChemicalIndustries, Ltd.) using hexane and ethyl acetate as eluate, the oilybrown material was fined to obtain 7.5 g (yield: about 62%) of an oily,pale yellow material represented by the following chemical formula.

¹H-NMR(CDCl₃):δ1.21(t,6H),4.10-4.19(m,8H),5.69(dd,1H),6.28(dd,1H),6.36-6.43(m,1H)

IR(NaCl):2985,2941,2909,1747,1659,1621,1462,1409,1374,1352,1295,1259,1193,1097,1070,1026,972,869,796,734,641,558cm⁻¹

Example 6

15.0 g (200 mmol) of 2-methylamino)ethanol was added to 200 ml ofdehydrated dichloromethane in a flask followed by Ar gas replacement.Thereafter, 24.3 g (240 mmol) of triethyl amine was added thereto. Next,the system was cooled down to about −10° C. 18.1 g (200 mmol) of acrylicacid chloride was slowly dropped in the system while keeping thetemperature in the system ranged from −10° C. to −5° C. and thereafterstirred for two hours at room temperature. Furthermore, subsequent toremoval of precipitants by filtration, the filtrate was washed withsaturated sodium hydrogen carbonate aqueous solution and saturatedsodium chloride aqueous solution. Next, subsequent to drying by sodiumsulfate, the dried resultant was condensed under a reduced pressure toobtain an oily brown material. Furthermore, by a column chromatographyfilled with 300 g of Wakogel C300 (manufactured by Wako Pure ChemicalIndustries, Ltd.) using hexane and ethyl acetate as eluate, the oilybrown material was fined to obtain 7.9 g (yield: about 30%) of an oily,transparent material represented by the following chemical formula.

¹H-NMR(CDCl₃):δ3.02(s,1.5H),3.15(s,1.5H),3.52(t,1H),3.60(t,1H),3.73-3.83(m,2H),5.62-5.75(m,1H),6.23-6.34(m,1H),6.55-6.74(m,1H)

IR(NaCl):3391,2937,2879,1645,1606,1486,1452,1420,1406,1359,1259,1211,1116,1052,981,862,796,748,609cm⁻¹

Example 7

140 ml of dehydrated tetrahydrofuran was added to 6.1 g (140 mmol) ofsodium hydride in a flask followed by Ar gas replacement. Thereafter, asolution in which 14.3 g (100 mmol) of 2-(cyclohexylamino)ethanol wasdissolved in 50 ml of tetrahydrofuran was slowly dropped in the flask atroom temperature and the system was stirred for 24 hours at roomtemperature. Next, after 21.8 g (140 mmol) of ethyl iodide was slowlyadded while being cooled in water, the system was stirred at roomtemperature for 24 hours. Furthermore, after filtration, the filtratewas condensed. Next, 100 ml of ethyl acetate was added to the system,the resultant was washed with water. Furthermore, subsequent to dryingby sodium sulfate, the dried resultant was condensed under a reducedpressure to obtain 14.7 g (yield: about 86%) of an oily orange materialrepresented by the following chemical formula.

¹H-NMR(CDCl₃):δ0.80-0.90(m,1H),1.00-1.30(m,8H),1.62(d,1H),1.73(d,2H),1.88(d,2H),2.38-2.45(m,1H),2.80(t,2H),3.49(t,2H),3.55(t,2H)

IR(NaCl):2974,2927,2854,1449,1378,1348,1260,1228,1115,890,835,760,533cm⁻¹7.7 g (45 mmol) of the oily orange material was added to 100 ml ofdehydrated dichlormethane in a flask followed by Ar gas replacement.Thereafter, 6.6 g (65 mmol) of triethyl amine was added thereto. Next,the system was cooled down to about −10° C. 4.9 g (54 mmol) of acrylicacid chloride was slowly dropped in the system while keeping thetemperature in the system ranged from −10° C. to −5° C. and thereafterstirred at a room temperature for two hours. Furthermore, subsequent toremoval of precipitants by filtration, the filtrate was washed withsaturated sodium hydrogen carbonate aqueous solution and saturatedsodium chloride aqueous solution. Next, subsequent to drying by sodiumsulfate, the dried resultant was condensed under a reduced pressure toobtain an oily brown material. Furthermore, by a column chromatographyfilled with 300 g of Wakogel C300 (manufactured by Wako Pure ChemicalIndustries, Ltd.) using hexane and ethyl acetate as eluate, the oilybrown material was fined to obtain 5.1 g (yield: about 50%) of an oily,pale yellow material represented by the following chemical formula.

¹H-NMR(CDCl₃):δ1.11(qd 1H),1.17-1.23(d3H),1.25-1.48(m,3H),1.55(q,1H),1.62-1.89(m,5H),3.40-3.60(m,6H),3.66(t,1H),5.66(t,1H),6.23-6.38(dd,1H),6.55-6.69(m,1H)

IR(NaCl):2974,2931,2857,1650,1611,1468,1427,1351,1301,1261,1238,1147,1115,1058,980,895,795cm⁻¹

Example 8

After 11.8 g (60 mmol) of pentacarbonyl iron was added to 360 ml of 0.5N ethanol solution of potassium hydroxide at a room temperature, 5.4 g(60 mmol) of 2-ethoxyethyl amine and 6.4 g (60 mmol) of benzaldehydewere further added at a room temperature followed by stirring for 24hours. Next, the system was stirred for three hours at about 50° C.followed by filtration. Furthermore, after concentration of thefiltrate, 100 ml of ethyl acetate was added. Next, after being washedwith water, the resultant was condensed to obtain 7.9 g (yield: about73%) of an oily brown material represented by the following chemicalformula.

¹H-NMR(CDCl₃):δ1.19 (t,3H),1.77 (br,1H),2.80(t,2H),3.48(q,2H),3.55(t,2H), 3.81(s,2H)

IR(NaCl):3027,2974,2866,1495,1453,1376,1114,1028,735,698cm⁻¹

7.2 g (40 mmol) of the oily orange material was added to 100 ml ofdehydrated dichlormethane in a flask followed by Ar gas replacement.Thereafter, 5.9 g (58 mmol) of triethyl amine was added thereto. Next,the system was cooled down to about −10° C. 4.3 g (48 mmol) of acrylicacid chloride was slowly dropped in the system while keeping thetemperature in the system ranged from −10° C. to −5° C. and thereafterstirred for two hours at room temperature. Furthermore, subsequent toremoval of precipitants by filtration, the filtrate was washed withsaturated sodium hydrogen carbonate aqueous solution and saturatedsodium chloride aqueous solution. Next, subsequent to drying by sodiumsulfate, the dried resultant was condensed under a reduced pressure toobtain an oily brown material. Furthermore, by a column chromatographyfilled with 300 g of Wakogel C300 (manufactured by Wako Pure ChemicalIndustries, Ltd.) using hexane and ethyl acetate as eluate, the oilybrown material was fined to obtain 3.9 g (yield: about 42%) of an oily,pale yellow material represented by the following chemical formula.

¹H-NMR(CDCl₃):δ1.16(t,3H),3.43(q,2H),3.47(s,2H),3.63(s,2H),4.73(d,2H),5.69(dd,1H),6.40(dd,1H),6.50-6.78(m,1H),7.15-7.36(m,5H)

IR(NaCl):3063,3030,2975,2932,2869,1651,1614,1495,1443,1356,1262,1221,1117,1060,1030,979,793,733,699,518cm⁻¹

Example 9

5.8 g (132 ml) of sodium hydride was added to 140 ml of dehydratedtetrahydrofuran in a flask followed by Ar gas replacement. Thereafter, asolution in which 14.2 g (110 mmol) of 2-(2-hydroxyethyl)piperidine wasdissolved in 50 ml of tetrahydrofuran was slowly dropped in the flask atroom temperature and the system was stirred for 24 hours at roomtemperature. Next, after 17.2 g (110 mmol) of ethyl iodide was slowlyadded while being cooled in water, the system was stirred at roomtemperature for 24 hours. Furthermore, after filtration, the filtratewas condensed. Next, 100 ml of ethyl acetate was added to the system,the resultant was washed with water. Furthermore, subsequent to dryingby sodium sulfate, the dried resultant was condensed under a reducedpressure to obtain 11.7 g (yield: about 67%) of an oily brown materialrepresented by the following chemical formula.

Molecule peak (M+) of MS spectrum (tetrahydrofuran (THF solution): 228IR (NaCl): 3300,2931,2856,1743,1444,1375,1239,1115,1048,748,558 cm-1.Since THF (molecular weight: 72) was attached to the molecule ion, themolecule ion peak of the oily brown material (molecular weight: 157)means 156.

10.9 g (69 mmol) of the oily brown material was added to 100 ml ofdehydrated dichlormethane in a flask followed by Ar gas replacement.Thereafter, 10.1 g (100 mmol) of triethyl amine was added thereto. Next,the system was cooled down to about −10° C. 7.6 g (84 mmol) of acrylicacid chloride was slowly dropped in the system while keeping thetemperature in the system ranged from −10° C. to −5° C. and thereafterstirred for two hours at room temperature. Furthermore, subsequent toremoval of precipitants by filtration, the filtrate was washed withsaturated sodium hydrogen carbonate aqueous solution and saturatedsodium chloride aqueous solution. Next, subsequent to drying by sodiumsulfate, the dried resultant was condensed under a reduced pressure toobtain an oily brown material.

Furthermore, by a column chromatography filled with 300 g of WakogelC300 (manufactured by Wako Pure Chemical Industries, Ltd.) using hexaneand ethyl acetate as eluate, the oily brown material was fined to obtain4.9 g (yield: about 33%) of an oily, pale yellow material represented bythe following chemical formula.

¹H-NMR (CDCl₃):δ1.18(t,3H),1.42(br,1H),1.60-1.80(m,6H),2.01-2.12(br,1H),2.62(t,1H),3.20-3.30(m,1H),3.36-3.50(m,4H),4.32(br,1H),4.60(d,11I),5.64(dd,1H),6.26-6.33(m,1H),6.70-6.80(m,1H)

IR(NaCl):2974,2935,2864,2801,1645,1607,1440,1377,1356,1333,1262,1212,1177,1137,1114,1057,1031,997,955,894,865,836,791,648cm⁻¹

Example 10

9.5 g (83 mmol) of 4-methoxy piperidine was added to 100 ml ofdehydrated dichlormethane in a flask followed by Ar gas replacement.Thereafter, 12.0 g (119 mmol) of triethyl amine was added thereto. Next,the system was cooled down to about −10° C. 9.0 g (99 mmol) of acrylicacid chloride was slowly dropped in the system while keeping thetemperature in the system ranged from −10° C. to −5° C. and thereafterstirred for two hours at room temperature. Furthermore, subsequent toremoval of precipitants by filtration, the filtrate was washed withsaturated sodium hydrogen carbonate aqueous solution and saturatedsodium chloride aqueous solution. Next, subsequent to drying by sodiumsulfate, the dried resultant was condensed under a reduced pressure toobtain an oily brown material. Furthermore, by a column chromatographyfilled with 300 g of Wakogel C300 (manufactured by Wako Pure ChemicalIndustries, Ltd.) using hexane and ethyl acetate as eluate, the oilybrown material was fined to obtain 7.2 g (yield: about 53%) of an oily,pale yellow material represented by the following chemical formula.

¹H-NMR(CDCl₃):δ1.54-1.62(m,2H),1.83-1.90(m,2H),3.36(s,3H),3.31-3.49(m,3H),3.75(br,1H),3.93(br,1H),5.67(dd,1H),6.25(dd,1H),6.56-6.63(m,1H)

IR(NaCl):2946,2877,2825,1646,1610,1444,1365,1343,1317,1263,1226,1193,1098,1079,1023,980,940,884,791,744,668,558cm⁻¹

Example 11

6.0 g (60 mmol) of 1-methyl piperidine was added to 100 ml of dehydrateddichlormethane in a flask followed by Ar gas replacement. Thereafter,9.1 g (90 mmol) of triethyl amine was added thereto. Next, the systemwas cooled down to about −10° C. 6.5 g (72 mmol) of acrylic acidchloride was slowly dropped in the system while keeping the temperaturein the system ranged from −10° C. to −5° C. and thereafter stirred fortwo hours at room temperature. Furthermore, subsequent to removal ofprecipitants by filtration, the filtrate was washed with saturatedsodium hydrogen carbonate aqueous solution and saturated sodium chlorideaqueous solution. Next, subsequent to drying by sodium sulfate, thedried resultant was condensed under a reduced pressure to obtain an oilybrown material.

Furthermore, by a column chromatography filled with 300 g of WakogelC300 (manufactured by Wako Pure Chemical Industries, Ltd.) using hexaneand ethyl acetate as eluate, the oily brown material was fined to obtain2.9 g (yield: about 31%) of an oily, pale yellow material represented bythe following chemical formula.

¹H-NMR(CDCl₃):δ2.31(s,3H),3.40 (t,4H),3.60(br,2H),3.71(br,2H), 5.70(d1H),6.28(d,1H),6.54-6.20(m,1H)

IR(NaCl):2940,2850,2794,1647,1610,1445,1366,1337,1293,1254,1230,1172,1144,1074,1041,1002,980,790,749,573cm⁻¹

Example 12

9.4 g (65 mmol) of 1-(2-methoxyethyl)piperazine was added to 100 ml ofdehydrated dichlormethane in a flask followed by Ar gas replacement.Thereafter, 9.5 g (94 mmol) of triethyl amine was added thereto. Next,the system was cooled down to about −10° C. 7.1 g (78 mmol) of acrylicacid chloride was slowly dropped in the system while keeping thetemperature in the system ranged from −10° C. to −5° C. and thereafterstirred for two hours at room temperature. Furthermore, subsequent toremoval of precipitants by filtration, the filtrate was washed withsaturated sodium hydrogen carbonate aqueous solution and saturatedsodium chloride aqueous solution. Next, subsequent to drying by sodiumsulfate, the dried resultant was condensed under a reduced pressure toobtain an oily brown material. Furthermore, by a column chromatographyfilled with 300 g of Wakogel C300 (manufactured by Wako Pure ChemicalIndustries, Ltd.) using hexane and ethyl acetate as eluate, the oilybrown material was fined to obtain 6.8 g (yield: about 53%) of an oily,pale yellow material represented by the following chemical formula.

¹H-NMR(CDCl₃):δ2.51(t,4H),2.60(t,2H),3.36(s,3H)3.52(t,2H),3.59(br,2H),3.72(br,2H),5.69(d,1H),6.28(d,1H),6.52-6.60(m,1H)

IR(NaCl):2925,2877,2815,1650,1613,1441,1365,1351,1307,1236,1151,1115,1071,1041,1021,1005,963,844,791cm⁻¹

Example 13

4.1 g (31 mmol) of 1-piperazine ethanol was added to 100 ml ofdehydrated dichlormethane in a flask followed by Ar gas replacement.Thereafter, 3.7 g (37 mmol) of triethyl amine was added thereto. Next,the system was cooled down to about −10° C. 2.8 g (31 mmol) of acrylicacid chloride was slowly dropped in the system while keeping thetemperature in the system ranged from −10° C. to −5° C. and thereafterstirred for two hours at room temperature. Furthermore, after removal ofprecipitate by filtration, the filtrate was condensed under a reducedpressure followed by addition of 150 ml of acetone. Next, after removingprecipitate by filtration, the filtrate was condensed to obtain 4.3 g ofa viscous matter. Furthermore, after 1.6 g (37 mmol) of 55% sodiumhydride (containing liquid paraffin) was washed with dehydratedtetrahydrofuran, 40 ml of dehydrated tetrahydrofuran was added and 4.3 gof the viscous matter were thereafter added followed by stirring at roomtemperature for one hour. Next, 9.4 g (60 mmol) of ethyl iodide wasadded thereto followed by stirring for 16 hours at room temperature.Thereafter, the system was heated at 66° C. for three hours.Furthermore, after removal of precipitate by filtration, the filtratewas condensed under a reduced pressure to obtain 4.2 g of an oily yellowmaterial.

Furthermore, by a column chromatography filled with 200 g of WakogelC300 (manufactured by Wako Pure Chemical Industries, Ltd.) using acetoneand hexane as eluate, the oily yellow material was fined to obtain 0.8 g(yield: about 12%) of an oily, transparent material represented by thefollowing chemical formula.

¹H-NMR(CDCl₃):δ1.20(t,3H),2.52(br,4H),2.61(t,2H),3.51(q,2H)3.57(t,2H),3.58(br,2H),3.71(br,2H),5.69(d,1H),6.28(d,1H),6.53-6.59(m,1H)

IR(NaCl):2973,2932,2867,2811,1727,1674,1646,1611,1442,1387,1351,1304,1238,1112,1041,1016,1002,980,792cm⁻¹

Example 14

39.1 g (300 mmol) of 1-piperazine ethanol was added to 250 ml ofdehydrated dichlormethane in a flask followed by Ar gas replacement.Thereafter, 36.4 g (360 mmol) of triethyl amine was added thereto. Next,the system was cooled down to about −10° C. 26.3 g (290 mmol) of acrylicacid chloride was slowly dropped in the system while keeping thetemperature in the system ranged from −10° C. to −5° C. and thereafterstirred for two hours at room temperature. Furthermore, after removal ofprecipitate by filtration, the filtrate was condensed under a reducedpressure followed by an addition of 300 ml of acetone and the resultantwas preserve in a refrigerator. Furthermore, after removal ofprecipitate by filtration, the filtrate was condensed under a reducedpressure to obtain 40 g of an oily orange material.

Furthermore, by a column chromatography filled with 300 g of WakogelC300 (manufactured by Wako Pure Chemical Industries, Ltd.) using acetoneand methanol as eluate, the oily orange material was fined to obtain 7.5g of an oily, pale yellow material represented by the following chemicalformula.

¹H-NMR (CDCl₃):δ2.54(t,4H),2.59(t,2H),2.66(br,1H),3.59(br,2H),3.66(t,2H),3.72(br,2H),5.71(d,1H),6.29(d,1H),6.54-6.59(m,1H)

IR(NaCl):3391,2945,2820,1734,1643,1606,1446,1366,1305,1249,1148,1052,1012,1000,979,910,875,792,767,751cm⁻¹

4.6 g (25 mmol) of the oily, pale yellow material was added to 70 ml ofdehydrated dichlormethane in a flask followed by Ar gas replacement.Thereafter, 4.1 g (40 mmol) of triethyl amine was added thereto. Next,the system was cooled down to about −10° C. 2.8 g (30 mmol) of propionicacid chloride was slowly dropped in the system while keeping thetemperature in the system ranged from −10° C. to −5° C. and thereafterstirred for two hours at room temperature. Furthermore, after removal ofprecipitate by filtration, the filtrate was condensed under a reducedpressure followed by an addition of 100 ml of ethyl acetate forextraction. The resultant was condensed under a reduced pressure toobtain 6.1 g of oily yellow material. Furthermore, by a columnchromatography filled with 200 g of Wakogel C300 (manufactured by WakoPure Chemical Industries, Ltd.) using acetone and ethyl acetate aseluate, the oily brown material was fined to obtain 3.1 g (yield: about52%) of an oily, pale yellow material represented by the followingchemical formula.

¹H-NMR(CDCl₃):δ1.14(t,3H),2.34(q,2H),2.52(t,4H),2.66(t,2H),3.57(br,2H),3.70(br,2H),4.22(t,2H),5.69(d,1H),6.28(d,1H),6.53-6.59(m,1H)

IR(NaCl):2943,2817,1736,1647,1611,1444,1368,1347,1307,1235,1187,1085,1017,1004,972,791cm⁻¹

Example 15

6.3 g (40 mmol) of 1-piperazine ethylcarbonate was added to 100 ml ofdehydrated dichlormethane in a flask followed by Ar gas replacement.Thereafter, 6.1 g (60 mmol) of triethyl amine was added thereto. Next,the system was cooled down to about −10° C. 4.3 g (48 mmol) of acrylicacid chloride was slowly dropped in the system while keeping thetemperature in the system ranged from −10° C. to −5° C. and thereafterstirred for two hours at room temperature. Furthermore, subsequent toremoval of precipitants by filtration, the filtrate was washed withsaturated sodium hydrogen carbonate aqueous solution and saturatedsodium chloride aqueous solution. Next, subsequent to drying by sodiumsulfate, the dried resultant was condensed under a reduced pressure toobtain an oily brown material.

Furthermore, by a column chromatography filled with 300 g of WakogelC300 (manufactured by Wako Pure Chemical Industries, Ltd.) using hexaneand ethyl acetate as eluate, the oily brown material was fined to obtain4.1 g (yield: about 48%) of an oily, pale yellow material represented bythe following chemical formula.

¹H-NMR(CDCl₃):δ1.28(t,3H),3.47-3.53(m,4H),3.55(br,2H),3.67(br,2H),4.16(q,4H),5.73(dd,1H),6.31(dd,1H),6.53-6.61(m,1H)

IR(NaCl):2983,2909,2865,1703,1651,1614,1434,1385,1354,1281,1232,1173,1126,1082,1033,990,924,872,825,791,768,543cm⁻¹

Example 16

12.6 g (80 mmol) of ethyl nipecotiate was added to 100 ml of dehydrateddichloromethane in a flask followed by Ar gas replacement. Thereafter,11.6 g (115 mmol) of triethyl amine was added thereto. Next, the systemwas cooled down to about −10° C. 8.7 g (96 mmol) of acrylic acidchloride was slowly dropped in the system while keeping the temperaturein the system ranged from −10° C. to −5° C. and thereafter stirred fortwo hours at room temperature.

Furthermore, subsequent to removal of precipitants by filtration, thefiltrate was washed with saturated sodium hydrogen carbonate aqueoussolution and saturated sodium chloride aqueous solution. Next,subsequent to drying by sodium sulfate, the dried resultant wascondensed under a reduced pressure to obtain an oily brown material.

Furthermore, by a column chromatography filled with 300 g of WakogelC300 (manufactured by Wako Pure Chemical Industries, Ltd.) using hexaneand ethyl acetate as eluate, the oily brown material was fined to obtain9.1 g (yield: about 53%) of an oily, pale yellow material represented bythe following chemical formula.

¹H-NMR(CDCl₃):δ1.26(s,2H),1.43-1.59(m,1H),1.63-1.88(m,2H),2.00-2.20(m2H),2.44-2.54(m,1H),3.06-3.24(m,1H),3.48-3.58(m,1H),3.82-3.94(d,1H),4.14(q,2H), 5.69(d,1H),6.27(d,1H),6.53-6.71(m,1H)

IR(NaCl):2981,2941,2863,1731,1650,1614,1442,1378,1301,1255,1226,1179,1120,1030,1009,978,857,791,623cm⁻¹

Example 17

7.9 g (50 mmol) of 4-piperidine ethylcarbonate was added to 100 ml ofdehydrated dichlormethane in a flask followed by Ar gas replacement.Thereafter, 7.3 g (72 mmol) of triethyl amine was added thereto. Next,the system was cooled down to about −10° C. 5.4 g (60 mmol) of acrylicacid chloride was slowly dropped in the system while keeping thetemperature in the system ranged from −10° C. to −5° C. and thereafterstirred for two hours at room temperature.

Furthermore, subsequent to removal of precipitants by filtration, thefiltrate was washed with saturated sodium hydrogen carbonate aqueoussolution and saturated sodium chloride aqueous solution. Next,subsequent to drying by sodium sulfate, the dried resultant wascondensed under a reduced pressure to obtain an oily brown material.Furthermore, by a column chromatography filled with 300 g of WakogelC300 (manufactured by Wako Pure Chemical Industries, Ltd.) using hexaneand ethyl acetate as eluate, the oily brown material was fined to obtain5.4 g (yield: about 51%) of an oily, pale yellow material represented bythe following chemical formula.

¹H-NMR(CDCl₃):δ1.26(t,3H),1.70(m,2H),1.94(m,2H),2.56(m,1H),2.91(t,1H),3.16(t,1H),3.90(d,1H),4.14(m,2H),4.44(d,1H),5.67(dd,1H),6.25(dd,1H),6.54-6.61(m,1H)

IR(NaCl):3475,2981,2956,2862,1729,1646,1611,1448,1377,1316,1264,1179,1097,1042,980,950,921,863,792,619,526cm⁻¹

Comparative Example 1

Acryloyl morpholine represented by the following chemical formula,available on the market, was used.

Comparative Example 2

N—N-diethylacrylamide represented by the following chemical formula,available on the market, was used.

Comparative Example 3

N-(3-dimethylaminopropyl)acrylamide represented by the followingchemical formula, available on the market, was used.

Comparative Example 4

N-(2-hydroxyethyl)acrylamide represented by the following chemicalformula, available on the market, was used.

Comparative Example 5

N—N′-methylene bisacrylamide represented by the following chemicalformula, available on the market, was used.

Comparative Example 6

9.1 g (50 mmol) of dicyclohexyl amine was added to 100 ml of dehydrateddichloromethane in a flask followed by Ar gas replacement. Thereafter,7.3 g (72 mmol) of triethyl amine was added thereto. Next, the systemwas cooled down to about −10° C. 5.4 g (60 mmol) of acrylic acidchloride was slowly dropped in the system while keeping the temperaturein the system ranged from −10° C. to −5° C. and thereafter stirred fortwo hours at room temperature. Furthermore, subsequent to removal ofprecipitants by filtration, the filtrate was washed with saturatedsodium hydrogen carbonate aqueous solution and saturated sodium chlorideaqueous solution. Next, subsequent to drying by sodium sulfate, thedried resultant was condensed under a reduced pressure to obtain an oilybrown material. Furthermore, by a column chromatography filled with 300g of Wakogel C300 (manufactured by Wako Pure Chemical Industries, Ltd.)using hexane and ethyl acetate as eluate, the oily brown material wasfined to obtain 8.0 g (yield: about 68%) of a pale yellow crystalrepresented by the following chemical formula.

¹H-NMR(CDCl₃):δ1.01-1.04(m,8H),1.05-1.08(m,12H),2.89(br,1H),3.51(br,1H),5.56(d,1H),6.18(d,1H),6.80-6.90(m,1H)

IR(NaCl):3095,2930,2854,1646,1607,1469,1439,1396,1350,1303,1264,1237,1224,1184,1145,1126,1055,1028,995,979,952,895,844,820,791,756,677,614cm⁻¹

Comparative Example 7

5.3 g (40 mmol) of 1,2,3,4-tetrahydroisoquinoline was added to 100 ml ofdehydrated dichloromethane in a flask followed by Ar gas replacement.Thereafter, 6.1 g (60 mmol) of triethyl amine was added thereto. Next,the system was cooled down to about −10° C. 4.3 g (48 mmol) of acrylicacid chloride was slowly dropped in the system while keeping thetemperature in the system ranged from −10° C. to −5° C. and thereafterstirred for two hours at room temperature. Furthermore, subsequent toremoval of precipitants by filtration, the filtrate was washed withsaturated sodium hydrogen carbonate aqueous solution and saturatedsodium chloride aqueous solution. Next, subsequent to drying by sodiumsulfate, the dried resultant was condensed under a reduced pressure toobtain an oily brown material.

Furthermore, by a column chromatography filled with 300 g of WakogelC300 (manufactured by Wako Pure Chemical Industries, Ltd.) using hexaneand ethyl acetate as eluate, the oily brown material was fined to obtain3.9 g (yield: about 54%) of an oily yellow material represented by thefollowing chemical formula.

1H-NMR(CDCl3):δ2.84-2.94(m,2H),3.82(dt,2H),4.76(d,2H),5.72(d,1H),6.33(d,1H),6.60-6.70(m, 1H),7.06-7.24(m,4H)

IR(NaCl):3023,2928,2898,2842,1650,1613,1583,1496,1444,1384,1365,1346,1294,1278,1245,1211,1111,1055,1038,977,933,828,792,763,745,660,600,568cm⁻¹

Comparative Example 8

5.3 g (40 mmol) of 1,2,3,4-tetrahydroisoquinoline was added to 100 ml ofdehydrated dichloromethane in a flask followed by Ar gas replacement.Thereafter, 6.1 g (60 mmol) of triethyl amine was added thereto. Next,the system was cooled down to about −10° C. 5.0 g (48 mmol) ofmethacrylic acid chloride was slowly dropped in the system while keepingthe temperature in the system ranged from −10° C. to −5° C. andthereafter stirred for two hours at room temperature. Furthermore,subsequent to removal of precipitants by filtration, the filtrate waswashed with saturated sodium hydrogen carbonate aqueous solution andsaturated sodium chloride aqueous solution. Next, subsequent to dryingby sodium sulfate, the dried resultant was condensed under a reducedpressure to obtain an oily brown material. Furthermore, by a columnchromatography filled with 300 g of Wakogel C300 (manufactured by WakoPure Chemical Industries, Ltd.) using hexane and ethyl acetate aseluate, the oily brown material was fined to obtain 5.2 g (yield: about68%) of an oily yellow material represented by the following chemicalformula.

¹H-NMR(CDCl₃):δ1.99(s,3H),2.88(s,2H),3.80(d,2H),4.74(d,21-1),5.09(s,1H), 5.23(s,1H),7.00-7.25(m,4H)

IR(NaCl):3081,3022,2976,2921,2843,1647,1622,1584,1497,1435,1371,1343,1302,1277,1247,1182,1110,1055,1039,1015,981,929,826,754,628,557cm⁻¹

Comparative Example 9

6.0 g (60 mmol) of 1-methyl piperidine was added to 100 ml of dehydrateddichloromethane in a flask followed by Ar gas replacement. Thereafter,9.1 g (90 mmol) of triethyl amine was added thereto. Next, the systemwas cooled down to about −10° C. 7.5 g (72 mmol) of methacrylic acidchloride was slowly dropped in the system while keeping the temperaturein the system ranged from −10° C. to −5° C. and thereafter stirred fortwo hours at room temperature.

Furthermore, subsequent to removal of precipitants by filtration, thefiltrate was washed with saturated sodium hydrogen carbonate aqueoussolution and saturated sodium chloride aqueous solution. Next,subsequent to drying by sodium sulfate, the dried resultant wascondensed under a reduced pressure to obtain an oily brown material.Furthermore, by a column chromatography filled with 300 g of WakogelC300 (manufactured by Wako Pure Chemical Industries, Ltd.) using hexaneand ethyl acetate as eluate, the oily brown material was fined to obtain5.7 g (yield: about 56%) of an oily yellow material represented by thefollowing chemical formula.

¹H-NMR(CDCl₃):δ1.96(s,3H),2.32(s,3H),2.41(br,4H),3.50-3.80(br,4H),5.03(br,1H),5.19(br,1H)

IR(NaCl):3081,2972,2939,2847,2791,2742,1650,1626,1462,1434,1370,1303,1290,1246,1203,1172,1142,1072,1038,1002,912,779,616,561cm⁻¹

Comparative Example 10

6.3 g (40 mmol) of 1-piperazine ethylcarbonate was added to 100 ml ofdehydrated dichloromethane in a flask followed by Ar gas replacement.Thereafter, 6.1 g (60 mmol) of triethyl amine was added thereto. Next,the system was cooled down to about −10° C. 5.0 g (48 mmol) ofmethacrylic acid chloride was slowly dropped in the system while keepingthe temperature in the system ranged from −10° C. to −5° C. andthereafter stirred for two hours at room temperature. Furthermore,subsequent to removal of precipitants by filtration, the filtrate waswashed with saturated sodium hydrogen carbonate aqueous solution andsaturated sodium chloride aqueous solution. Next, subsequent to dryingby sodium sulfate, the dried resultant was condensed under a reducedpressure to obtain an oily brown material.

Furthermore, by a column chromatography filled with 300 g of WakogelC300 (manufactured by Wako Pure Chemical Industries, Ltd.) using hexaneand ethyl acetate as eluate, the oily brown material was fined to obtain7.3 g (yield: about 81%) of an oily, pale yellow material represented bythe following chemical formula.

¹H-NMR(CDCl₃):δ1.29(t,3H),1.96(t,3H),3.48(br,4H),3.57(br,4H),4.17(q,2H), 5.04(d,1H),5.22(d,1H)

IR(NaCl):3082,2982,2916,2864,1698,1650,1622,1470,1430,1386,1355,1283,1253,1233,1198,1174,1125,1080,1030,1006,990,918,870,826,769,596,562,541cm⁻¹

Manufacturing of Photopolymerizable Composition

950 mg of the photopolymerizable compounds of Examples and ComparativeExamples and 50 mg of a photopolymerization initiator (IRGACURE 907:2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropane-1-one,manufactured by BASF Japan Ltd.) were mixed by a magnetic stirrer toprepare photopolymerizable compositions.

Next, the viscosity and the odor of the photopolymerizable compoundswere evaluated.

In addition, using the photopolymerizable compound, thephotopolymerizability and photocurability of the photopolymerizablecompound were evaluated.

Viscosity

Using a viscoelasticity measuring instrument VAR200AD, manufactured byREOLOGICA, the viscosity of the photopolymerizable compound at 25° C.was measured. A plate of having a diameter of 40 mm was used for themeasuring.

Odor

The odor of the photopolymerizable compound was evaluated according tothe following procedure. The criteria of evaluating the odor of thephotopolymerizable compound are as follows:

-   A: Order sensed but not uncomfortable-   B: Uncomfortable peculiar odor-   C: Particularly uncomfortable peculiar odor-   (1): About 100 g (0.1 g) of a photopolymerizable compound was    weighed and put in a 50 cc glass bottle and the lid thereof was    closed.-   (2): The glass bottle was left at room temperature for about 30    minutes.-   (3): Thereafter, the lid was opened to smell the odor by nose.

Photopolymerizability

The photopolymerizability of the photopolymerizable compound wasmeasured by using a measuring instrument formed by a combination ofDSC-7020 (manufactured by Seiko Instruments Inc.) and a spot lightsource LA-410 UV (manufactured by Hayashi Watch-Works Co., Ltd.) forevaluation. Specifically, the amount of generated heat was measured forone sample when the photopolymerizable compound in thephotopolymerizable composition was exposed to ultraviolet ray having awavelength of 365 nm with 200 mW/cm² for a sufficient time to completepolymerization. The generated heat obtained in the measuring includedthe generated heat accompanied by ultraviolet irradiation in addition tothe heat generated accompanied by the polymerization of thephotopolymerizable compound.

Therefore, to the sample which had been polymerized for measuring, thesample was exposed to ultraviolet ray again under the same condition tomeasure the amount of generated heat other than the amount of generatedheat accompanied by the polymerization of the photopolymerizablecompound. The amount of generated heat accompanied by the polymerizationof the photopolymerizable compound from the difference between theamounts of generated heat for the first time and the second time. T₁(s),which was defined as the time from the start of irradiation ofultraviolet ray to when the amount of generated heat reached themaximum, was used as an index to compare the speed ofphotopolymerization.

Photocurability

The photocurability of the photopolymerizable compound was evaluated byusing a measuring instrument formed by a combination of aviscoelasticity measuring instrument (VAR 200 AD, manufactured byREOLOGICA) and an LED light source (LIGHTNINGCURE LC-L1, manufactured byHamamatsu Photonics K.K.). Specifically, after nipping aphotopolymerizable composition with a gap of 10 μm using a cone platehaving a diameter of 20 mm, the photopolymerizable composition wasexposed to ultraviolet ray having a wavelength of 365 nm with 50 mW/cm²to measure the change of the elasticity thereof until the elasticity wassaturated. Based on the measuring results, the maximum value of theelasticity was obtained, which was defined as index of curing level.Normally, when a material has a coefficient of elasticity of 1×10⁴ Pa,the curing level thereof is said to be sufficient. In addition, theenergy of ultraviolet ray to which the compound is exposed until thecoefficient of elasticity is saturated, i.e., curing energy, iscalculated by multiplying an intensity (50 mW/cm²) of ultraviolet raywith irradiation time (s) of ultraviolet ray.

The evaluation results of the viscosity, the odor, thephotopolymerizability, and the photocurability of the photopolymerizablecompounds are shown in Table 1.

TABLE 1 Photo- Photo-curability poly- Curing Viscosity merizabilityElasticity energy (mPa · s) Odor T1 (s) (×10⁵ Pa) (mJ/cm²) Example 1 2 A5.4 1.0 321 Example 2 3 A 4.8 0.9 428 Example 3 4 A 3.6 0.8 382 Example4 4 A 5.4 1.0 309 Example 5 46 A 5.4 1.0 232 Example 6 27 A 3.6 1.0 119Example 7 12 A 3.6 1.0 128 Example 8 21 A 5.0 1.0 300 Example 9 11 A 3.61.0 147 Example 10 9 A 4.9 1.0 265 Example 11 6 A 5.1 1.0 280 Example 1213 A 4.8 1.0 158 Example 13 9 A 3.6 0.7 250 Example 14 86 A 3.0 1.0 130Example 15 81 A 4.2 1.0 130 Example 16 13 A 3.0 1.0 110 Example 17 12 A2.8 1.0 101 Comparative 6 B 6.5 1.0 190 Example 1 Comparative 2 C 4.81.0 208 Example 2 Comparative 70 C 3.6 1.0 244 Example 3 Comparative 128A — — — Example 4 Comparative — B — — — Example 5 Comparative — A — — —Example 6 Comparative 436 A 7.0 1.0 2,744   Example 7 Comparative 505 A— — — Example 8 Comparative 6 A — — — Example 9 Comparative 410 A — — —Example 10

As seen in Table 1, the photopolymerizable compounds of Examples 1 to 17had excellent photopolymerizability and photocurability with less odorand viscosity.

However, the photopolymerizable compound of Comparative Example 1 hadodor since it had a morpholino group.

The photopolymerizable compound of Comparative Example 2 had odorsignificantly because it had no carbonyl imino group or polar group inthe ethyl group bonded with a nitrogen atom.

The photopolymerizable compound of Comparative Example 3 had odorsignificantly because it had a carbonyl imino group and a dimethyl aminogroup.

Since the photopolymerizable compound of Comparative Example 4 had acarbonyl imino group and a hydroxyl group so that the viscosity thereofwas high, the photopolymerization initiator was not dissolved in thephotopolymerizable compound, thereby failing to obtain aphotopolymerizable composition.

Since the photopolymerizable compound of Comparative Example 5 had twocarbonyl imino groups, it was solid at room temperature, so that aphotopolymerizable composition was not manufactured.

Since the photopolymerizable compound of Comparative Example 6 had nocarbonyl imino group and the two cyclohexane groups were bonded by anitrogen atom, it was solid at room temperature, so that aphotopolymerizable composition was not manufactured.

Since the photopolymerizable compounds of Comparative Examples 7 and 8had no carbonyl imino group and a monovalent group containing a polargroup was not bonded to a ring containing a nitrogen atom, thephotopolymerizable compound had a high viscosity and low curability.

The photopolymerizable compounds of Comparative Examples 8 to 10 weremethacrylic amides, it was not photopolymerized, so that no photocuringoccurred.

Since the nitrogen atom in the photopolymerizable compound ofComparative Example 10 was replaced with an ethyloxycarbonyl group, ithad a high viscosity.

Preparation of Ink

100 parts of the photopolymerizable compounds of Examples 1 to 17, 10parts of a photopolymerization initiator (IRGACURE 907, manufactured byBASF Japan), and 3 parts of carbon black MICROLITH Black C-K(manufactured by BASF Japan) were mixed to obtain Ink 1.

100 parts of the photopolymerizable compounds of Examples 1 to 17, 10parts of a photopolymerization initiator (IRGACURE 907, manufactured byBASF Japan), and 3 parts of carbon black MICROLITH Blue 4G-K(manufactured by BASF Japan) were mixed to obtain Ink 2.

Evaluation of Ink 1

After discharging ink on a slide glass, the ink was exposed toultraviolet ray having a wavelength of 365 nm with 200 mW/cm² using a UVirradiator LH6 (manufactured by Heraeus Noblelight Fusion UV) forcuring.

As a consequence, it was confirmed Ink 1 and 2 were dischargeable andthe ink images were sufficiently cured.

Evaluation of Ink 2

The tip of a dip pen was dipped in ink and texts were written on a PETfilm and plain paper. Thereafter, the texts were exposed to ultravioletray having a wavelength of 365 nm with 200 mW/cm² using a UV irradiatorLH6 (manufactured by Heraeus Noblelight Fusion UV) for curing. As aconsequence, it was confirmed the ink images of Ink 1 and 2 weresufficiently cured.

According to the present disclosure, a compound, ink and a compositionthat contain the ink, which have excellent polymerization property andphoto-curability with less odor and small viscosity are provided.

Having now fully described embodiments of the present invention, it willbe apparent to one of ordinary skill in the art that many changes andmodifications can be made thereto without departing from the spirit andscope of embodiments of the invention as set forth herein.

What is claimed is:
 1. Ink comprising: at least one of a compound represented by chemical formula 1, a compound represented by chemical formula 2, a compound represented by chemical formula 3, or a compound represented by chemical formula 4,

where R₁ represents a hydrocarbon group having 1 to 10 carbon atoms and R₂ represents a monovalent group comprising one functional group selected from the group consisting of a group represented by —COOX₂, where X₂ represents a monovalent hydrocarbon group having 1 to 10 carbon atoms, a group represented by —OCOX₃, where X₃ represents a monovalent hydrocarbon group having 1 to 10 carbon atoms, and a group represented by —NX₄X₅, where X₄ and X₅ each, independently represent monovalent hydrocarbon groups having 1 to 10 carbon atoms,

where, R₃ and R₄ each, independently represent monovalent groups comprising groups represented by —OX₁, where X₁ represents a monovalent hydrocarbon group having 1 to 10 carbon atoms, a monovalent group comprising a group represented by —COOX₂, where X₂ represents a monovalent hydrocarbon group having 1 to 10 carbon atoms, a monovalent group comprising a group represented by —OCOX₃, where X₃ represents a monovalent hydrocarbon group having 1 to 10 carbon atoms, a monovalent group comprising a group represented by —NX₄X₅, where X₄ and X₅ each, independently represent monovalent hydrocarbon groups having 1 to 10 carbon atoms, a monovalent group comprising a group represented by —CONX₆X₇, where X₆ and X₇ each, independently represent monovalent hydrocarbon groups having 1 to 10 carbon atoms, or a monovalent group comprising a hydroxyl group,

where a ring A represents a saturated five-membered ring or a saturated six-membered ring, both comprising a nitrogen atom, R₅ represents a monovalent group comprising a group represented by —OX₁, where X₁ represents a monovalent hydrocarbon group having 1 to 10 carbon atoms, a monovalent group comprising a group represented by —COOX₂, where X₂ represents a monovalent hydrocarbon group having 1 to 3 carbon atoms other than a t-butyl group, a monovalent group comprising a group represented by —OCOX₃, where X₃ represents a monovalent hydrocarbon group having 1 to 10 carbon atoms, a monovalent group comprising a group represented by —NX₄X₅, where X₄ and X₅ each, independently represent monovalent hydrocarbon groups having 1 to 10 carbon atoms, a monovalent group comprising a group represented by —CONX₆X₇, where X₆ and X₇ each, independently represent monovalent hydrocarbon groups having 1 to 10 carbon atoms, or a monovalent group comprising a hydroxyl group, and a is 1, 2, or 3, and

where a ring B represents a saturated five-membered ring or a saturated six-membered ring, both comprising two nitrogen atoms, R₆ represents a monovalent group comprising a group represented by —OX₁, where X₁ represents a monovalent hydrocarbon group having 1 to 10 carbon atoms, a monovalent group comprising a group represented by —COOX₂, where X₂ represents a monovalent hydrocarbon group having 1 to 10 carbon atoms, a monovalent group comprising a group represented by —OCOX₃, where X₃ represents a monovalent hydrocarbon group having 1 to 10 carbon atoms, a monovalent group comprising a group represented by —NX₄X₅, where X₄ and X₅ each, independently represent monovalent hydrocarbon groups having 1 to 10 carbon atoms, a monovalent group comprising a group represented by —CONX₆X₇, where X₆ and X₇ each, independently represent monovalent hydrocarbon groups having 1 to 10 carbon atoms, a monovalent group comprising a hydroxyl group, or an alkyl group having 1 to 10 carbon atoms, wherein, in each of Chemical Formula 2, 3, and 4, when R₃, R₄, and R₆ represents —OX₁, —OX₁ is bound to the nitrogen atom through an alkylene group that has at least three carbon atoms, and a viscosity of the ink ranges from 7 mPa·s to 30 mPa·s.
 2. The ink according to claim 1, wherein the ink comprises the compound represented by chemical formula 1, wherein R₁ represents a cycloalkyl group, an aryl group, or an aralkyl group.
 3. The ink according to claim 1, wherein R₃ and R₄ each independently represent 2-hydroxyethyl group.
 4. The ink according to claim 1, wherein the ink comprises the compound represented by chemical formula 3, which is represented by chemical formula 6


5. The ink according to claim 4, wherein R₅ is a group represented by —COOX₂, where X₂ represents a hydrocarbon group having 1 to 10 carbon atoms other than a t-butyl group.
 6. An ink cartridge comprising: the ink of claim 1; and a container to accommodate the ink.
 7. An ink jet recording device comprising: a discharging device comprising the ink of claim 1 to discharge the ink.
 8. An ink jet ink printed matter comprising: an image of the ink of claim 1; and a recording medium on which the image is formed.
 9. The ink according to claim 1, which further comprises at least one of: a photopolymerization initiator; and a colorant.
 10. The ink according to claim 1, which further comprises: a photopolymerization initiator; and a colorant.
 11. The ink according to claim 1, wherein the ink comprises the compound represented by chemical formula 4, wherein, in formula 4, the nitrogen atom of ring B bound to R₆ is bound to R₆ through a —(CH₂)_(m)— linker group, where m represents an integer of from 1 to
 6. 12. The ink according to claim 1, wherein the ink comprises the compound represented by chemical formula 3, wherein in formula 3, a is 2 or
 3. 13. The ink according to claim 1, wherein the ink does not comprise a solvent.
 14. The ink according to claim 1, wherein the ink comprises an organic solvent in an amount of from 0.1% by weight to 5% by weight. 